25047-22-7

Basic information

• Product Name: O-diacetyl-(+/-)-α-conidendrine
• CAS NO: 25047-22-7
• Molecular Weight: 440.45
• Mol File: 25047-22-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-diacetyl-(+/-)-α-conidendrine(CAS DataBase Reference)
• NIST Chemistry Reference: O-diacetyl-(+/-)-α-conidendrine(25047-22-7)
• EPA Substance Registry System: O-diacetyl-(+/-)-α-conidendrine(25047-22-7)

Safety Data

• Hazardous Substances Data: 25047-22-7(Hazardous Substances Data)

Upstream product

• 71724-97-5 (1S,3aR,4S,9aR)-4-(4'-acetoxy-3'-methoxyphenyl)-1,7-dimethoxy-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-yl acetate 
• 101312-79-2 (1S,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol 
• 127951-04-6 (+/-)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-05-7 (2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-05-7 (+/-)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (+/-)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-01-3 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 911805-41-9 (+/-)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-00-2 (3R)-(+)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-00-2 (+/-)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 84755-40-8 (hydroxy-4 methoxy-3 benzyl)-4 dihydro-3H-furannone-2 
• 140193-27-7 (-)-O-6-Benzyl-α-conidendrine 

Downstream Products

• 133553-64-7 Acetic acid 4-(4-acetoxy-3-methoxy-phenyl)-7-methoxy-1-oxo-1,3-dihydro-naphtho[2,3-c]furan-6-yl ester 

Relevant articles and documents

-

(-)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl-γ-butyrolactone (R)-(+)-4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding silyl ethers 10, with O-benzylvanillyl bromide 11, gave the trans disubstituted lactones 13 (2 epimers). Catalytic hydrogenolysis (Pd-C) of 13 selectively split the aryl benzyl ether linkage, and gave the compounds 14. Intramolecular Friedel-Crafts cyclization of the latter, using the benzyloxy group as the leaving group, was induced with BF3-Et2O and afforded (-)-α-conidendrin 1 in 36% overall yield from methyl α-vanillylhemis uccinate (R)-(+)-17.

ETUDES DE LIGNANES 7 - SYNTHESES TOTALES DES (+-)-α ET -β-CONIDENDRINES ET DES METHYL (+-)-α ET -β-CONIDENDRALS

Michael addition of the carbanion of the dithian 8 on butenolide, followed by alkylation with the benzylic bromide 11 and regeneration of the ketonic carbonyl group, gave the α,β-disubstituted lactone 13.Reduction of the ketonic carbonyl of the latter usi